Cabin holiday rentals in Highland Lake

What a treat to stay at McCaela's magical, cozy, home! Everything – from the surroundings, to the furnishings, to the amenities – were just perfect. Entry into the house was no problem, and inside we found a delightfully thoughtful and intentional home that was extremely comfortable and spotlessly clean. Just as key, the bed in the primary bedroom was supremely comfortable! We had no reason to ask any questions, and we had no issues at all; still, McCaela reached out to make sure we were settled and to see if we needed anything. We SO appreciated her generosity, kindness, and insight into (and commitment to) the local community. It's clear that a great deal of thought and care has gone into this house, and we would stay there again in a heartbeat. The location is perfect – off the beaten path and extremely private, yet close to everything we wanted in the Berkshires. I highly recommend staying here, ideally for longer than the two nights we did. We can't wait to return!

Amazing stay in the forest! Cozy, peaceful, and super romantic. Perfect place to relax, disconnect, and enjoy nature. Thank you for the unforgettable experience!

Michelle's Hilltop Cabin in Chesterfield, MA, is a wonderful place. Nestled in the Berkshire woods, but close to the road, and not far from civilization, this place has all the best western Massachusetts has to offer. 11 miles (15 minutes) to Snow Farm (Williamsburg) 17 miles (28 minutes) to downtown Northampton 23 miles (36 minutes) to UMass Amherst 31 miles (44 minutes) to Mass MOCA (North Adams) 32 miles (51 minutes) to Tanglewood (Lenox) The Hilltop Cabin is best for 2-3 people, but Michelle has several other rentals at the same address. See if she has openings to suit your party on your dates. You won't be disappointed!

The space is luxurious and stunning even more beautiful than the photos, so thoughtfully designed and really helped us feel at home at once. Matt and Sarah were so helpful whenever we had any questions. We had such a relaxing stay and feel so grateful to have been able to enjoy the space!

We had an amazing time at Ruth’s home and we loved the cabin feel. Between the hot tub, lake, and lawn games our time went by so quickly. The home was very clean and had all the essentials. We will definitely be back again!

Pictures don’t do it justice! The place is super adorable and relaxing. Great views and vibes. Personal touches that make you feel like you’re visiting a friends home instead of an Airbnb. Highly recommend!

The place is overall awesome - just don’t miss the fact there isn’t air conditioning - I didn’t notice that in the listing, and there happened to be a hot day. The hot tub isn’t quite private. One set of neighbors or folks turning down the side road can see you. However, it was very comfortable, especially on a cool evening.

My boyfriend and I stayed here for a peaceful weekend away and it was soo worth it. The home is so clean and updated and it was so nice. The bath towels were thick and smelled amazing! It really is the little details that made this place stand out to me. And the creek running in the back is so serene. I would absolutely stay here again. It rained most of our stay but we were so warm and cozy inside. I would love to come back during a sunny weekend to explore more of the outdoors, because the Catskills mountains are so amazing.

Great little cabin in the woods. This was exactly what I was looking for. Quaint, quiet, and located on a lake.

We absolutely loved our stay at this cozy, charming cabin! It’s the perfect place to unplug and unwind. Nestled in a peaceful, quiet setting, the cabin feels like a true retreat from everyday life. We especially enjoyed the screened-in porch for morning coffee and evening chats. The nearby waterfalls (a 30–40 minute walk or 10-minute drive) were a wonderful way to enjoy the area’s natural beauty. The two-person soaking tub was a highlight—so relaxing after a hike! The cabin is thoughtfully equipped with a small but functional kitchen, which made it easy to prepare simple meals. We also appreciated the high-quality linens and comfortable bed—such a nice touch that made our stay feel special. While it’s ideal for unplugging, there is Wi-Fi if you need it. There are also some cute towns nearby, full of antique shops and local charm. It was the perfect blend of nature, comfort, and low-key exploration. We’re already dreaming of our next visit!

Nothing but great things to say about this Airbnb. The house was absolutely beautiful and so cozy. The kitchen was extremely well stocked with pretty much everything you need. The hosts were also incredibly helpful and responded right away whenever we had questions or issues with anything. Highly recommend this Airbnb. I hope to come back one day!

amazing! both the host and the house. secluded feeling. magical!

Emily and Carol were wonderful hosts. They were responsive to our questions and provided great recommendations. Sitting on the balcony with the view of the trees and the lake beyond was tranquil. The living area is cozily furnished and both the fireplace and tv were easy to use. The nearby community beach was fun to visit and an added benefit of the stay. Great location with plenty of good food and small town charm!

The guesthouse was so dreamy! We had a wonderful stay, the hosts were super friendly, and we loved meeting their sweet dogs. The house was close to great restaurants and shops in Hudson, Kinderhook, and Ghent, as well as hiking trails. The lovely trail on the property was a great bonus, one we took advantage of 4 times throughout the weekend :). Would definitely visit again!

We loved staying at Lucy’s. It’s one of those places that has everything you need, from extra blankets, lots of silverware, to high quality WiFi. And the surrounding area is beautiful.

Bob is an absolutely amazing host and is incredibly communicative - he was always looking to ensure that we were enjoying our stay and that any issues were remedied as quickly as possible. The home was exactly as described: immaculately clean, very comfortable beds, and full of thoughtful touches that made us feel right at home. It was raining quite a bit during our stay, but the amazing view from Bob’s cabin was more than enough to make up for the bad weather. We wouldn’t hesitate to stay here again and highly recommend this place to anyone visiting the area!

It was a perfect price. With the ABNB it was double+. I would rather pay John more for the one night personally, than what I did. And have done twice. I have always left the place the same or better than I found it. I understand the cleaning fee, but kills single fathers like me for a 1 night trip. That being said. Walker cabin is great! Kayaks, all safety gear, fully outfitted down to toothpicks, brushes, floss, ect. You think you forgot it. It’s there. Baby monitors!

Really enjoyed our stay! Was perfect for our family to stay all in one place. Darin responded in a timely manner and was very helpful. Pool table was a great addition! Loved the location, it was beautiful & peaceful. We were disappointed we didn't see any bears :0) LOL

We loved our stay in Jeremy and Danielle’s cabin. It was warm and cozy and rustic yet modern. The place was in pristine condition, and we felt immediately at home upon entering. We will definitely rent it again the next time we are in the area. :-)

Great for a weekend away with my friends and I!!! Looks exactly like the pictures and was listed for an AMAZING price for everything that we got! Would totally come back and could not recommend enough!!!

Lanthe and Josephine’s cabin was an absolute dream. From the moment we arrived, we felt completely at peace. The space is warm, thoughtfully decorated, and nestled in such a serene location, perfect for a quiet getaway from the city. Everything was clean, cozy, and exactly as pictured. You can truly feel the love and care that went into creating this space. It was the perfect setting to relax, reconnect, and make meaningful memories. Thank you both for being such gracious and welcoming hosts. We’re already looking forward to returning!

Thank you Mariana for allowing me to stay in your beautiful cottage. I needed to step away from my life for a few days and this was the perfect place. Quiet, private, just lovely interior. Decor is incredibly soothing, I’ve never stayed in an Airbnb or any rental that had thought of so many details. Anything you needed, anything you forgot to bring it was here. One of my favorite places I’ve ever stayed, actually teared up in gratitude as I left which I’ve never done!! Thank you so much

Really cool cabin- all the other reviewers said it perfectly! Super clean, stylish and modern.

I booked this Airbnb for a crew working on a nearby project. John’s instructions included lack of cell service, remote location, darkness and stairs outside, a home filled with antiques …. all worrisome to me handing this place over to people I didn’t know. Each one told me it was perfect, and each for a different reason! One loved the furnishings, one loved the rural feel, one loved the architecture … everyone felt it was a special treat at the end of long days of physical labor. Great experience.